Water → 4-Chloro-2-methyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729266Notes

Reaction equation

HRID 729266 reaction equation
[Cl:1][C:2]1[C:3](=[O:15])[NH:4][S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI.[C:18](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:3](=[O:15])[N:4]([CH3:18])[S:5](=[O:13])(=[O:14])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68661656HCID 68661656, compound

Product 1

HCID 686620174-Chloro-2-methyl-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 104%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (2.0 g, 8.21 mmol) and MeI (3.5 g, 24.6 mmol) in DMF (30 ml) was cooled with an ice bath, and anhydrous potassium carbonate (1.13 g, 8.21 mmol) was added. The mixture was then allowed to warm to rt and stirred for 21 h. Water (60 ml) was added and the white precipitate formed, was filtered off and washed with water. Toluene was added to the precipitate and the mixture was evaporated and the residue was dried for three days under vacuum to give the title compound (2.2 g, 102%) containing traces of water and toluene. 1H NMR (400 MHz, CDCl3): δ 3.23 (s, 3H), 7.52-7.56 (m, 3H), 7.86-7.88 (m, 2H); 13C-NMR (100 MHz, CD3CN): δ 24.5, 123.8, 1291, 129.5, 130.7, 133.0, 143.1, 157.6.

Workup

  1. customthe white precipitate formed
  2. filtrationwas filtered off
  3. washwashed with water
  4. additionToluene was added to the precipitate
  5. customthe mixture was evaporated
  6. customthe residue was dried for three days under vacuum

Sources & evidence

ORD record
ord-45c600a773ac4635ba9a18c0d831f33a
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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